IL212830A - Carbamate derivatives of alkyl-heterocycles, their preparation, and their medical use - Google Patents

Carbamate derivatives of alkyl-heterocycles, their preparation, and their medical use

Info

Publication number: IL212830A
Authority: IL; Israel
Prior art keywords: group; mmol; general formula; compound; alkyl
Prior art date: 2008-11-14

Application number

IL212830A

Other languages

English (en)

Hebrew (he)

Other versions

IL212830A0 (en

Original Assignee

Sanofi Sa

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2008-11-14

Filing date

2011-05-11

Publication date

2014-11-30

Family has litigation

First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=40852115&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=IL212830(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.

2011-05-11 Application filed by Sanofi Sa filed Critical Sanofi Sa

2011-07-31 Publication of IL212830A0 publication Critical patent/IL212830A0/en

2014-11-30 Publication of IL212830A publication Critical patent/IL212830A/en

Links

238000002360 preparation method Methods 0.000 title claims description 11
230000001225 therapeutic effect Effects 0.000 title description 5
150000004657 carbamic acid derivatives Chemical class 0.000 title description 4
-1 -CH2CN Chemical group 0.000 claims description 208
150000001875 compounds Chemical class 0.000 claims description 195
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 29
150000003839 salts Chemical class 0.000 claims description 26
239000002904 solvent Substances 0.000 claims description 23
125000005843 halogen group Chemical group 0.000 claims description 22
238000006243 chemical reaction Methods 0.000 claims description 15
229910052731 fluorine Chemical group 0.000 claims description 15
125000003373 pyrazinyl group Chemical group 0.000 claims description 15
125000001153 fluoro group Chemical group F* 0.000 claims description 14
125000001424 substituent group Chemical group 0.000 claims description 13
NXLNNXIXOYSCMB-UHFFFAOYSA-N (4-nitrophenyl) carbonochloridate Chemical compound [O-][N+](=O)C1=CC=C(OC(Cl)=O)C=C1 NXLNNXIXOYSCMB-UHFFFAOYSA-N 0.000 claims description 12
229910052801 chlorine Inorganic materials 0.000 claims description 12
239000000460 chlorine Substances 0.000 claims description 12
125000002098 pyridazinyl group Chemical group 0.000 claims description 12
125000000714 pyrimidinyl group Chemical group 0.000 claims description 12
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 11
125000004076 pyridyl group Chemical group 0.000 claims description 11
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 11
150000001412 amines Chemical class 0.000 claims description 10
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
125000000842 isoxazolyl group Chemical group 0.000 claims description 9
125000001715 oxadiazolyl group Chemical group 0.000 claims description 9
125000002971 oxazolyl group Chemical group 0.000 claims description 9
125000003226 pyrazolyl group Chemical group 0.000 claims description 9
125000001113 thiadiazolyl group Chemical group 0.000 claims description 9
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 8
206010028980 Neoplasm Diseases 0.000 claims description 8
208000002193 Pain Diseases 0.000 claims description 8
AKZWRTCWNXHHFR-PDIZUQLASA-N [(3S)-oxolan-3-yl] N-[(2S,3S)-4-[(5S)-5-benzyl-3-[(2R)-2-carbamoyloxy-2,3-dihydro-1H-inden-1-yl]-4-oxo-3H-pyrrol-5-yl]-3-hydroxy-1-phenylbutan-2-yl]carbamate Chemical compound NC(=O)O[C@@H]1Cc2ccccc2C1C1C=N[C@](C[C@H](O)[C@H](Cc2ccccc2)NC(=O)O[C@H]2CCOC2)(Cc2ccccc2)C1=O AKZWRTCWNXHHFR-PDIZUQLASA-N 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 8
125000003118 aryl group Chemical group 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
125000002883 imidazolyl group Chemical group 0.000 claims description 8
230000007170 pathology Effects 0.000 claims description 8
125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 8
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 8
125000004306 triazinyl group Chemical group 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
125000002541 furyl group Chemical group 0.000 claims description 7
238000010992 reflux Methods 0.000 claims description 7
125000001425 triazolyl group Chemical group 0.000 claims description 7
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
230000001154 acute effect Effects 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000004429 atom Chemical group 0.000 claims description 5
125000000753 cycloalkyl group Chemical group 0.000 claims description 5
239000003814 drug Substances 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
125000001786 isothiazolyl group Chemical group 0.000 claims description 5
239000000546 pharmaceutical excipient Substances 0.000 claims description 5
125000004193 piperazinyl group Chemical group 0.000 claims description 5
125000000168 pyrrolyl group Chemical group 0.000 claims description 5
125000001544 thienyl group Chemical group 0.000 claims description 5
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
230000009471 action Effects 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
230000001684 chronic effect Effects 0.000 claims description 4
125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 4
125000001072 heteroaryl group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
208000027866 inflammatory disease Diseases 0.000 claims description 4
125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 4
125000001624 naphthyl group Chemical group 0.000 claims description 4
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 4
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 4
239000000758 substrate Substances 0.000 claims description 4
125000003831 tetrazolyl group Chemical group 0.000 claims description 4
208000000094 Chronic Pain Diseases 0.000 claims description 3
206010028813 Nausea Diseases 0.000 claims description 3
208000005298 acute pain Diseases 0.000 claims description 3
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
208000035475 disorder Diseases 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
230000008693 nausea Effects 0.000 claims description 3
239000008194 pharmaceutical composition Substances 0.000 claims description 3
230000002685 pulmonary effect Effects 0.000 claims description 3
229910052723 transition metal Inorganic materials 0.000 claims description 3
150000003624 transition metals Chemical class 0.000 claims description 3
HEAHLTGDUHXTTO-UHFFFAOYSA-N 1,3-thiazolidine 1,1-dioxide Chemical compound O=S1(=O)CCNC1 HEAHLTGDUHXTTO-UHFFFAOYSA-N 0.000 claims description 2
IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 claims description 2
FBXGQDUVJBKEAJ-UHFFFAOYSA-N 4h-oxazin-3-one Chemical compound O=C1CC=CON1 FBXGQDUVJBKEAJ-UHFFFAOYSA-N 0.000 claims description 2
208000024172 Cardiovascular disease Diseases 0.000 claims description 2
208000030814 Eating disease Diseases 0.000 claims description 2
208000019454 Feeding and Eating disease Diseases 0.000 claims description 2
101100134927 Gallus gallus COR8 gene Proteins 0.000 claims description 2
208000018522 Gastrointestinal disease Diseases 0.000 claims description 2
208000001132 Osteoporosis Diseases 0.000 claims description 2
206010063897 Renal ischaemia Diseases 0.000 claims description 2
206010046543 Urinary incontinence Diseases 0.000 claims description 2
208000012886 Vertigo Diseases 0.000 claims description 2
206010047700 Vomiting Diseases 0.000 claims description 2
208000026935 allergic disease Diseases 0.000 claims description 2
XYOVOXDWRFGKEX-UHFFFAOYSA-N azepine Chemical compound N1C=CC=CC=C1 XYOVOXDWRFGKEX-UHFFFAOYSA-N 0.000 claims description 2
HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 claims description 2
208000022362 bacterial infectious disease Diseases 0.000 claims description 2
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
235000014632 disordered eating Nutrition 0.000 claims description 2
239000002621 endocannabinoid Substances 0.000 claims description 2
206010015037 epilepsy Diseases 0.000 claims description 2
125000005945 imidazopyridyl group Chemical group 0.000 claims description 2
208000026278 immune system disease Diseases 0.000 claims description 2
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 2
125000001041 indolyl group Chemical group 0.000 claims description 2
125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 2
150000003951 lactams Chemical group 0.000 claims description 2
230000004770 neurodegeneration Effects 0.000 claims description 2
208000015122 neurodegenerative disease Diseases 0.000 claims description 2
230000000926 neurological effect Effects 0.000 claims description 2
LKZKGRRDUWVNSR-UHFFFAOYSA-N oxazepin-3-one Chemical group O=C1NOC=CC=C1 LKZKGRRDUWVNSR-UHFFFAOYSA-N 0.000 claims description 2
SFJGCXYXEFWEBK-UHFFFAOYSA-N oxazepine Chemical compound O1C=CC=CC=N1 SFJGCXYXEFWEBK-UHFFFAOYSA-N 0.000 claims description 2
230000003071 parasitic effect Effects 0.000 claims description 2
125000006085 pyrrolopyridyl group Chemical group 0.000 claims description 2
TVQOEGVBMRCMFR-UHFFFAOYSA-N thiadiazinane Chemical compound C1CNNSC1 TVQOEGVBMRCMFR-UHFFFAOYSA-N 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000004588 thienopyridyl group Chemical group S1C(=CC2=C1C=CC=N2)* 0.000 claims description 2
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 2
231100000889 vertigo Toxicity 0.000 claims description 2
230000003612 virological effect Effects 0.000 claims description 2
230000008673 vomiting Effects 0.000 claims description 2
101000918494 Homo sapiens Fatty-acid amide hydrolase 1 Proteins 0.000 claims 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 189
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
238000000034 method Methods 0.000 description 101
239000000243 solution Substances 0.000 description 93
239000000047 product Substances 0.000 description 90
239000000203 mixture Substances 0.000 description 79
238000005481 NMR spectroscopy Methods 0.000 description 70
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 64
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 48
230000008569 process Effects 0.000 description 45
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
239000000843 powder Substances 0.000 description 43
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 36
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 36
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
239000000741 silica gel Substances 0.000 description 33
229910002027 silica gel Inorganic materials 0.000 description 33
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 31
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 30
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 27
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 27
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 27
239000012074 organic phase Substances 0.000 description 27
229920006395 saturated elastomer Polymers 0.000 description 27
229910052938 sodium sulfate Inorganic materials 0.000 description 27
235000011152 sodium sulphate Nutrition 0.000 description 27
238000004587 chromatography analysis Methods 0.000 description 25
239000008346 aqueous phase Substances 0.000 description 24
239000011780 sodium chloride Substances 0.000 description 24
239000000706 filtrate Substances 0.000 description 22
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 19
239000012429 reaction media Substances 0.000 description 19
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 18
PCBZRNYXXCIELG-WYFCWLEVSA-N COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 Chemical compound COC1=CC=C(C[C@H](NC(=O)OC2CCCC3(C2)OOC2(O3)C3CC4CC(C3)CC2C4)C(=O)N[C@@H]2[C@@H](CO)O[C@H]([C@@H]2O)N2C=NC3=C2N=CN=C3N(C)C)C=C1 PCBZRNYXXCIELG-WYFCWLEVSA-N 0.000 description 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 16
238000000746 purification Methods 0.000 description 16
238000003756 stirring Methods 0.000 description 16
101150041968 CDC13 gene Proteins 0.000 description 15
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 15
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 14
238000001704 evaporation Methods 0.000 description 14
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 13
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 13
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
102100029111 Fatty-acid amide hydrolase 1 Human genes 0.000 description 11
108010046094 fatty-acid amide hydrolase Proteins 0.000 description 11
239000000543 intermediate Substances 0.000 description 11
239000007787 solid Substances 0.000 description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 10
229910000041 hydrogen chloride Inorganic materials 0.000 description 10
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 10
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 9
XFVSARIHJBMGIX-UHFFFAOYSA-N [3-(methylcarbamoyl)-1,2-oxazol-5-yl]methyl (4-nitrophenyl) carbonate Chemical compound O1N=C(C(=O)NC)C=C1COC(=O)OC1=CC=C([N+]([O-])=O)C=C1 XFVSARIHJBMGIX-UHFFFAOYSA-N 0.000 description 9
238000001914 filtration Methods 0.000 description 9
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
238000005160 1H NMR spectroscopy Methods 0.000 description 7
238000001035 drying Methods 0.000 description 7
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 6
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
235000019270 ammonium chloride Nutrition 0.000 description 6
230000002401 inhibitory effect Effects 0.000 description 6
GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 6
239000011535 reaction buffer Substances 0.000 description 6
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
201000010099 disease Diseases 0.000 description 5
238000006911 enzymatic reaction Methods 0.000 description 5
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 5
239000012453 solvate Substances 0.000 description 5
210000001519 tissue Anatomy 0.000 description 5
238000011282 treatment Methods 0.000 description 5
UVHSQARKEJDZDK-UHFFFAOYSA-N 2-[1-(6-chloroquinolin-2-yl)piperidin-4-yl]ethanamine Chemical compound C1CC(CCN)CCN1C1=CC=C(C=C(Cl)C=C2)C2=N1 UVHSQARKEJDZDK-UHFFFAOYSA-N 0.000 description 4
FZRBTBCCMVNZBD-UHFFFAOYSA-N 2-chloro-4-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=CC=NC(Cl)=N1 FZRBTBCCMVNZBD-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
238000005361 D2 NMR spectroscopy Methods 0.000 description 4
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IL212830A 2008-11-14 2011-05-11 Carbamate derivatives of alkyl-heterocycles, their preparation, and their medical use IL212830A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR0806371A FR2938537B1 (fr)	2008-11-14	2008-11-14	Derives de carbamates d'alkyl-heterocycles, leur preparation et leur application en therapeutique.
PCT/FR2009/052179 WO2010055267A1 (fr)	2008-11-14	2009-11-13	Derives de carbamates d'alkyl-heterocycles, leur preparation et leur application en therapeutique

Publications (2)

Publication Number	Publication Date
IL212830A0 IL212830A0 (en)	2011-07-31
IL212830A true IL212830A (en)	2014-11-30

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IL212830A IL212830A (en)	2008-11-14	2011-05-11	Carbamate derivatives of alkyl-heterocycles, their preparation, and their medical use

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US (1)	US8716289B2 (es)
EP (1)	EP2356108B1 (es)
JP (1)	JP5560287B2 (es)
KR (1)	KR20110083743A (es)
CN (1)	CN102216291B (es)
AR (1)	AR074119A1 (es)
AU (1)	AU2009315448B2 (es)
BR (1)	BRPI0921057A2 (es)
CA (1)	CA2743558C (es)
CL (1)	CL2011001122A1 (es)
CO (1)	CO6331472A2 (es)
CR (1)	CR20110246A (es)
EA (1)	EA019742B1 (es)
EC (1)	ECSP11011040A (es)
FR (1)	FR2938537B1 (es)
IL (1)	IL212830A (es)
MA (1)	MA32884B1 (es)
MX (1)	MX2011005124A (es)
NI (1)	NI201100095A (es)
NZ (1)	NZ592740A (es)
PA (1)	PA8848901A1 (es)
PE (1)	PE20120217A1 (es)
SV (1)	SV2011003895A (es)
TW (1)	TWI462919B (es)
UY (1)	UY32246A (es)
WO (1)	WO2010055267A1 (es)
ZA (1)	ZA201103516B (es)

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FR2934265B1 (fr) *	2008-07-23	2010-07-30	Sanofi Aventis	Derives de carbamates d'alkylthiazoles, leur preparation et leur application en therapeutique
US20130150346A1 (en)	2010-01-08	2013-06-13	Quest Ventures Ltd.	Use of FAAH Inhibitors for Treating Parkinson's Disease and Restless Legs Syndrome
US20130224151A1 (en)	2010-03-31	2013-08-29	United States Of America	Use of FAAH Inhibitors for Treating Abdominal, Visceral and Pelvic Pain
FR2960875B1 (fr)	2010-06-04	2012-12-28	Sanofi Aventis	Derives de carbamates d'hexafluoroisopropyle, leur preparation et leur application en therapeutique
GB201309508D0 (en) *	2013-05-28	2013-07-10	Redx Pharma Ltd	Compounds
ITMI20131180A1 (it)	2013-07-15	2015-01-16	Fond Istituto Italiano Di Tecnologia	O-alchil triazolil carbammati come inibitori di idrolasi delle ammidi degli acidi grassi (faah)
WO2016017467A1 (ja) *	2014-07-28	2016-02-04	住友化学株式会社	アミド化合物及びその有害節足動物防除用途
CN111171315B (zh) *	2020-02-25	2021-08-17	常熟理工学院	一种结晶性n-取代聚硫代氨基甲酸酯及其制备方法

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AU2003279877B2 (en) *	2002-10-07	2010-05-20	The Regents Of The University Of California	Modulation of anxiety through blockade of anandamide hydrolysis
FR2854633B1 (fr) *	2003-05-07	2005-06-24	Sanofi Synthelabo	Derives de piperidinyl-et piperazinyl-alkylcarbamates, leur preparation et leur application en therapeutique
CA2560700A1 (en)	2004-03-26	2005-10-06	Henrietta Dehmlow	Tetrahydrocarbazoles and derivatives
SE0401656D0 (sv)	2004-06-24	2004-06-24	Astrazeneca Ab	Chemical compounds
AU2005272389B2 (en) *	2004-08-11	2011-08-04	Kyorin Pharmaceutical Co., Ltd.	Novel cyclic aminobenzoic acid derivative
AU2006236387A1 (en) *	2005-04-18	2006-10-26	Neurogen Corporation	Subtituted heteroaryl CB1 antagonists
GB0510140D0 (en)	2005-05-18	2005-06-22	Addex Pharmaceuticals Sa	Novel compounds B2
WO2007146761A2 (en) *	2006-06-12	2007-12-21	Neurogen Corporation	Diaryl pyrimidinones and related compounds
KR101580482B1 (ko)	2007-11-16	2015-12-28	인사이트 홀딩스 코포레이션	야누스 키나제 억제제로서의 ４－피라졸릴－ｎ－아릴피리미딘－２－아민 및 ４－피라졸릴－ｎ－헤테로아릴피리미딘－２－아민
FR2934265B1 (fr) *	2008-07-23	2010-07-30	Sanofi Aventis	Derives de carbamates d'alkylthiazoles, leur preparation et leur application en therapeutique

2008
- 2008-11-14 FR FR0806371A patent/FR2938537B1/fr not_active Expired - Fee Related
2009
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- 2009-11-12 PA PA20098848901A patent/PA8848901A1/es unknown
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- 2009-11-13 US US13/129,235 patent/US8716289B2/en not_active Expired - Fee Related
- 2009-11-13 PE PE2011001013A patent/PE20120217A1/es not_active Application Discontinuation
- 2009-11-13 WO PCT/FR2009/052179 patent/WO2010055267A1/fr not_active Ceased
- 2009-11-13 JP JP2011543799A patent/JP5560287B2/ja not_active Expired - Fee Related
- 2009-11-13 EP EP09768186.0A patent/EP2356108B1/fr active Active
- 2009-11-13 EA EA201170686A patent/EA019742B1/ru not_active IP Right Cessation
- 2009-11-13 KR KR1020117013456A patent/KR20110083743A/ko not_active Ceased
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- 2009-11-13 AU AU2009315448A patent/AU2009315448B2/en not_active Ceased
- 2009-11-13 CA CA2743558A patent/CA2743558C/fr not_active Expired - Fee Related
2011
- 2011-05-05 SV SV2011003895A patent/SV2011003895A/es unknown
- 2011-05-10 CR CR20110246A patent/CR20110246A/es unknown
- 2011-05-11 CO CO11057594A patent/CO6331472A2/es not_active Application Discontinuation
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- 2011-05-11 NI NI201100095A patent/NI201100095A/es unknown
- 2011-05-13 ZA ZA2011/03516A patent/ZA201103516B/en unknown
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Also Published As

Publication number	Publication date
CR20110246A (es)	2012-06-15
CN102216291B (zh)	2016-08-03
SV2011003895A (es)	2011-08-15
WO2010055267A1 (fr)	2010-05-20
KR20110083743A (ko)	2011-07-20
US8716289B2 (en)	2014-05-06
NI201100095A (es)	2011-12-14
BRPI0921057A2 (pt)	2018-10-16
TWI462919B (zh)	2014-12-01
PE20120217A1 (es)	2012-03-12
EA019742B1 (ru)	2014-05-30
FR2938537A1 (fr)	2010-05-21
NZ592740A (en)	2013-03-28
AU2009315448A1 (en)	2010-05-20
IL212830A0 (en)	2011-07-31
MX2011005124A (es)	2011-05-30
AU2009315448B2 (en)	2015-07-16
JP2012508785A (ja)	2012-04-12
JP5560287B2 (ja)	2014-07-23
FR2938537B1 (fr)	2012-10-26
MA32884B1 (fr)	2011-12-01
CO6331472A2 (es)	2011-10-20
EP2356108B1 (fr)	2014-10-15
EA201170686A1 (ru)	2011-12-30
CA2743558C (fr)	2017-02-14
AR074119A1 (es)	2010-12-22
TW201026692A (en)	2010-07-16
CL2011001122A1 (es)	2011-09-16
CA2743558A1 (fr)	2010-05-20
US20120015950A1 (en)	2012-01-19
EP2356108A1 (fr)	2011-08-17
PA8848901A1 (es)	2010-06-28
UY32246A (es)	2010-06-30
ECSP11011040A (es)	2011-06-30
CN102216291A (zh)	2011-10-12
ZA201103516B (en)	2012-07-25

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AU2009274355B2 (en)	2014-01-30	Alkyl thiazole carbamate derivatives, preparation thereof, and use thereof as FAAH enzyme inhibitors
IL212830A (en)	2014-11-30	Carbamate derivatives of alkyl-heterocycles, their preparation, and their medical use
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AU2010247212B2 (en)	2015-07-16	5-membered heterocyclic compound cyclopenta[c]pyrrolylalkylcarbamate derivatives, preparation thereof, and therapeutic use thereof
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AU2011208418A1 (en)	2012-08-09	Alkyl-heterocycle carbamate derivatives, their preparation and their therapeutic application
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